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Questions and Answers
What is the primary focus concerning molecules with a C-C one-electron σ-bond?
What is the primary focus concerning molecules with a C-C one-electron σ-bond?
- Studying their thermal properties
- Determining their optimal synthesis method
- Achieving energy reversal between HOMO and SOMO states (correct)
- Evaluating their stability under different conditions
What condition is stated regarding the comparison of E1ox and E2ox in the proposed redox mechanisms?
What condition is stated regarding the comparison of E1ox and E2ox in the proposed redox mechanisms?
- E1ox is always lower than E2ox
- E2ox is always higher than E1ox
- E1ox is always equal to E2ox
- E1ox is greater than E2ox in some cases (correct)
Which statement accurately reflects the challenges mentioned in the research?
Which statement accurately reflects the challenges mentioned in the research?
- Reports on the desired molecules are extensive
- Optimal approaches for energy reversal remain elusive (correct)
- Energy reversal mechanisms are well understood
- Radical cation states have been thoroughly studied
What role do the HOMO and SOMO states play in the described energy reversal?
What role do the HOMO and SOMO states play in the described energy reversal?
In the context of the research, what does degradation refer to?
In the context of the research, what does degradation refer to?
What is implied about the research environment based on the affiliations listed?
What is implied about the research environment based on the affiliations listed?
Which of the following is a likely next step in the research according to the content?
Which of the following is a likely next step in the research according to the content?
What conclusion can be drawn about the ability to study HPE derivatives based on the content?
What conclusion can be drawn about the ability to study HPE derivatives based on the content?
What type of electron transfer is discussed in relation to 3,6-diaryl-2,6-octadienes?
What type of electron transfer is discussed in relation to 3,6-diaryl-2,6-octadienes?
Which chemical species is highlighted for its divergent reactivity based on electron-transfer conditions?
Which chemical species is highlighted for its divergent reactivity based on electron-transfer conditions?
What notable product formation is mentioned in relation to the rearrangements of the diketene compounds?
What notable product formation is mentioned in relation to the rearrangements of the diketene compounds?
Which method was confirmed by X-ray crystallography as mentioned in the document?
Which method was confirmed by X-ray crystallography as mentioned in the document?
Which year was the study on triphenylmethyl published in the Journal of the American Chemical Society?
Which year was the study on triphenylmethyl published in the Journal of the American Chemical Society?
What is the chemical characteristic of hexaphenylethane associated with strains?
What is the chemical characteristic of hexaphenylethane associated with strains?
Which concept relates to the isolation of a benzene valence isomer as per the document?
Which concept relates to the isolation of a benzene valence isomer as per the document?
What type of chemical bond did Suzuki et al. focus on in their study related to ultralong C–C bonds?
What type of chemical bond did Suzuki et al. focus on in their study related to ultralong C–C bonds?
What initial substance was combined with iodine in the synthesis of dication salt 12+(I3−)2?
What initial substance was combined with iodine in the synthesis of dication salt 12+(I3−)2?
What was the temperature maintained during the stirring process in the synthesis?
What was the temperature maintained during the stirring process in the synthesis?
What was the result after drying the resulting suspension of the synthesis?
What was the result after drying the resulting suspension of the synthesis?
What method was used for chromatography in the synthesis process?
What method was used for chromatography in the synthesis process?
What indication is given regarding the 1H NMR spectrum recorded during the synthesis?
What indication is given regarding the 1H NMR spectrum recorded during the synthesis?
What was the melting point range recorded for the synthesized solid?
What was the melting point range recorded for the synthesized solid?
What precursor was used to dry the acetonitrile before use in the experiment?
What precursor was used to dry the acetonitrile before use in the experiment?
Which analytical technique was employed to record the 13C NMR spectra?
Which analytical technique was employed to record the 13C NMR spectra?
What parameter is notable about the Csp3–Csp3 single bond in HPE 1?
What parameter is notable about the Csp3–Csp3 single bond in HPE 1?
Which structural feature of HPE 1 contributes to its oxidation process?
Which structural feature of HPE 1 contributes to its oxidation process?
What is the observed oxidation potential of the first step in the oxidation process of HPE 1?
What is the observed oxidation potential of the first step in the oxidation process of HPE 1?
What is a significant difference between the structures of 1 + and 12+?
What is a significant difference between the structures of 1 + and 12+?
For how long can crystals of 1 +I3− be stored under ambient conditions without decomposition?
For how long can crystals of 1 +I3− be stored under ambient conditions without decomposition?
What is the primary reason the naphthalene core does not facilitate stepwise oxidation in HPEs?
What is the primary reason the naphthalene core does not facilitate stepwise oxidation in HPEs?
What does the bond length of the C…C distance in HPE 1 indicate?
What does the bond length of the C…C distance in HPE 1 indicate?
What is indicated by the R indices (R1 and wR2) mentioned in relation to HPE 1?
What is indicated by the R indices (R1 and wR2) mentioned in relation to HPE 1?
What occurs at 110 K in relation to compound 1?
What occurs at 110 K in relation to compound 1?
What is the bond length of the C C one-electron σ-bond?
What is the bond length of the C C one-electron σ-bond?
Which of the following statements is true regarding the structural parameters?
Which of the following statements is true regarding the structural parameters?
What was the core structure of the B B one-electron bond based on?
What was the core structure of the B B one-electron bond based on?
What does the difference in interatomic distances suggest?
What does the difference in interatomic distances suggest?
What wavenumber (cm–1) corresponds to the C C symmetric vibration?
What wavenumber (cm–1) corresponds to the C C symmetric vibration?
What is observed at around 100 K related to the structural analysis?
What is observed at around 100 K related to the structural analysis?
The experimental data for Raman intensity is shown as a function of which parameter?
The experimental data for Raman intensity is shown as a function of which parameter?
Which aspect of the structure of 1 2+(I3−)2 is omitted for clarity?
Which aspect of the structure of 1 2+(I3−)2 is omitted for clarity?
What is noted about the thermal behavior of compounds at different temperatures?
What is noted about the thermal behavior of compounds at different temperatures?
What does the presence of disordered thermal ellipsoids indicate?
What does the presence of disordered thermal ellipsoids indicate?
Which experimental method is used to analyze the structures mentioned?
Which experimental method is used to analyze the structures mentioned?
What condition is NOT stated about the analysis conducted at 100 K?
What condition is NOT stated about the analysis conducted at 100 K?
What is indicated by the presence of the vibrational peak at 379 cm–1?
What is indicated by the presence of the vibrational peak at 379 cm–1?
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Study Notes
C-C One-Electron σ-Bond
- Molecules with a C-C one-electron σ-bond are elusive due to the difficulty of achieving an optimal energy reversal between the HOMO of the neutral state and the SOMO of the radical cation state.
- Electron-donating heteroatoms can help achieve this energy reversal.
HPE 1 Structure
- HPE 1, a molecule with two spiro-dibenzocycloheptatriene (DBCHT) units, has an elongated Csp3-Csp3 single bond (1.806(2) Å at 400 K).
- This elongated bond increases the HOMO level and results in a stepwise oxidation process.
X-ray Analysis of HPE 1
- X-ray analysis of HPE 1 revealed an unsymmetrical bent-planar structure with a C-C one-electron σ-bond with a bond length of 2.921(3) Å.
- The structure deviates from the typical planar conformation of a pimer composed of cationic and radical moieties or molecules.
- The observed structural difference is intrinsic and reproducible, confirmed by analyzing several single crystals of HPE 1 and its dication.
Raman Spectroscopy
- Raman spectroscopy confirms the presence of the C-C one-electron σ-bond by detecting a vibrational mode at 379 cm-1.
- This mode represents the symmetric vibration of the C-C one-electron σ-bond.
Synthesis of Dication Salt 12+(I3-)2
- Dication salt 12+(I3-)2 is synthesized by reacting HPE 1 with iodine in dry CH2Cl2.
- The resulting suspension is dried under reduced pressure to yield a dark violet solid.
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